Methyl iodide → HCID 13422332, compound

HRID 979235Notes

Reaction equation

HRID 979235 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=[O:19])[O:15][CH:16]([CH3:18])[CH3:17])[CH:5]=[C:6]([CH3:12])[C:7]=1[C:8](=[O:11])[CH2:9][CH3:10].I[CH3:21].[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:21][N:13]([C:4]1[CH:5]=[C:6]([CH3:12])[C:7]([C:8](=[O:11])[CH2:9][CH3:10])=[C:2]([CH3:1])[CH:3]=1)[C:14](=[O:19])[O:15][CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 13422322HCID 13422322, compound

Product 1

HCID 13422332HCID 13422332, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Isopropyl N-(3,5-dimethyl-4-propionylphenyl)carbamate (2.63 g) and iodomethane (4.30 g) were dissolved in tetrahydrofuran (10 ml). The resultant solution was dropwise added to a solution containing potassium hydroxide (1.68 g) and tetra-n-butylammonium bromide (1.0 g). After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with toluene. The extract was washed with water, dried over magnesiunm sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give isopropyl N-methyl-N-(3,5-dimethyl-4-propionylphenyl)carbamate (Compound No. 40) (2.60 g) in a yield of 93.8%. nD20.0 1.5120.

Workup

  1. extractionextracted with toluene
  2. washThe extract was washed with water
  3. dry with materialdried over magnesiunm sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. additiona mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-53e22554f3864b648d6ae04d262b45e2
Source dataset
uspto-grants-1987_05
Patent number
US04666938

Reaction notes

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